Synthesis ofα-Amino Acids Using Carbon Dioxide

• Project/Area Number: 22750081
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Hokkaido University
• Principal Investigator: MITA Tsuyoshi 北海道大学, 大学院・薬学研究院, 助教 (00548183)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000); Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: 二酸化炭素 / 固定化 / アミノ酸 / アミノスルホン / アミノスズ / フッ化セシウム / カルバニオン / フェニルグリシン

Research Abstract

Carbon dioxide is an abundant, inexpensive, and nontoxic C1 unit ; however, its inertness and gaseous character sometimes hamper its use for efficient C-C bond-forming reactions in organic synthesis. Despite its difficulty, we have successfully developed one-potα-amino acid synthesis from imines using carbon dioxide though C-C bond-formation.

Research Products

• [Journal Article] Synthesis of Arylglycine and Mandelic Acid Derivatives through Carboxylations ofα-Amido andα-Acetoxy Stannanes with Carbon Dioxide (2012)
  • Author(s): Mita, T.; Sugawara, M.; Hasegawa, H.; Sato, Y.
  • Journal Title: J. Org. Chem. Volume: 77 Issue: 5 Pages: 2159-2168
  • DOI: 10.1021/jo202597p
  • Peer Reviewed
• [Journal Article] Convenient and Practical Synthesis ofα-Amido Stannanes (2012)
  • Author(s): Mita, T.; Higuchi, Y.; Sato. Y.
  • Journal Title: Synthesis Volume: 44 Issue: 02 Pages: 194-200
  • DOI: 10.1055/s-0031-1289597
  • Peer Reviewed
• [Journal Article] Practical Synthesis of N-Boc-and N-Cbz-α-Amido Stannanes fromα-Amido Sulfones Using TMSSnBu3 and CsF (2011)
  • Author(s): Mita, T.; Higuchi, Y.; Sato. Y.
  • Journal Title: Org. Lett. Volume: 13 Issue: 9 Pages: 2354-2357
  • DOI: 10.1021/ol200599d
  • Peer Reviewed
• [Journal Article] One-Pot Synthesis ofα-Amino Acids from Imines through CO_2 Incorporation : An Alternative Method for Strecker Synthesis (2011)
  • Author(s): Mita, T.; Chen, J.; Sugawara, M.; Sato, Y.
  • Journal Title: Angew. Chem., Int. Ed. Volume: 50 Issue: 6 Pages: 1393-1396
  • DOI: 10.1002/anie.201006422
  • Peer Reviewed
• [Journal Article] Practical Synthesis of N-Boc- and N-Cbz-α-Amido Stannanes from α-Amido Sulfones Using TMSSnBu_3 and CsF (2011)
  • Author(s): Tsuyoshi Mita
  • Journal Title: Org.Lett. Volume: 13 Pages: 2354-2357
  • Peer Reviewed
• [Journal Article] One-Pot Synthesis of α-Amino Acids from Imines through CO_2 Incorporation : An Alternative Method for Strecker Synthesis (2011)
  • Author(s): Tsuyoshi Mita
  • Journal Title: Angew.Chem., Int.Ed. Volume: 50 Pages: 1393-1396
  • Peer Reviewed
• [Presentation] 二酸化炭素ガスを用いたα-ヒドロキシカルボン酸類の新規合成法の開発 (2012)
  • Author(s): 美多剛
  • Organizer: 日本薬学会第132年会
  • Place of Presentation: 北海道大学(札幌)
  • Year and Date: 2012-03-30
• [Presentation] 二酸化炭素ガスを用いたα-ヒドロキシカルボン酸類の新規合成法の開発 (2012)
  • Author(s): 美多剛、長谷川裕之、菅原真純、佐藤美洋
  • Organizer: 日本薬学会第132回年会
  • Place of Presentation: 北海道大学(札幌)
• [Presentation] 酸化炭素ガスとフッ化セシウムを用いたα-アミノ酸の新規ワンポット合成法の開 (2011)
  • Author(s): 美多剛
  • Organizer: 第37回反応と合成の進歩シンポジウム
  • Place of Presentation: あわぎんホール(徳島)
  • Year and Date: 2011-11-08
• [Presentation] イミンと二酸化炭素ガスからのα-アミノ酸のワンポット合成 (2011)
  • Author(s): 美多剛
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川県横浜市神奈川大学
  • Year and Date: 2011-03-27
• [Presentation] Synthesis ofα-Amino Acid Derivatives by Means of CO_2 Fixation (2011)
  • Author(s): Tsuyoshi Mita, Jianyang Chen, Masumi Sugawara, Hiroyuki Hasegawa, Yoshihiro Sato
  • Organizer: 8th AFMC International Medicinal Chemistry Symposium-Frontier of Medicinal Science-
  • Place of Presentation: Keio Plaza Hotel(Tokyo)
• [Presentation] 二酸化炭素ガスとフッ化セシウムを用いたα-アミノ酸の新規ワンポット合成法の開発 (2011)
  • Author(s): 美多剛、陳建揚、菅原真純、長谷川裕之、佐藤美洋
  • Organizer: 第37回反応と合成の進歩シンポジウム-ライフサイエンスを志向した理論、反応および合成-
  • Place of Presentation: あわぎんホール(徳島)
• [Presentation] α-Amino Acid Synthesis through Carbon Dioxide Incorporation (2011)
  • Author(s): Tsuyoshi Mita, Masumi Sugawara, Jianyang Chen, Yoshihiro Sato
  • Organizer: The 16th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
  • Place of Presentation: Shanghai International Convention Center(China)
• [Presentation] イミンと二酸化炭素ガスからのα-アミノ酸のワンポット合成 (2011)
  • Author(s): 美多剛、陳建揚、菅原真純、佐藤美洋
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 神奈川大学(横浜)
• [Remarks] 研究室ホームページ
  • URL: http://gouka.pharm.hokudai.ac.jp/FSC/jpn/page/top_page.htm
• [Remarks]
• [Remarks]
  • URL: http://gouka.pharm.hokudai.ac.jp/FSC/jpn/page/top_page.htm
• [Patent(Industrial Property Rights)] α-アミノ酸塩の製造方法 (2011)
  • Inventor(s): 佐藤美洋、美多剛、宮地伸英
  • Industrial Property Rights Holder: 日産化学工業
  • Industrial Property Number: 2011-199151
  • Filing Date: 2011-09-13
• [Patent(Industrial Property Rights)] α-ヒドロキシ酸塩の製造方法 (2011)
  • Inventor(s): 佐藤美洋、美多剛、宮地伸英
  • Industrial Property Rights Holder: 日産化学工業
  • Industrial Property Number: 2011-187128
  • Filing Date: 2011-08-30
• [Patent(Industrial Property Rights)] α-アミノ酸塩の製造方法 (2011)
  • Inventor(s): 佐藤美洋
  • Industrial Property Rights Holder: 日産化学工業
  • Industrial Property Number: 2011-199151
  • Filing Date: 2011-09-13
• [Patent(Industrial Property Rights)] α-ヒドロキシ酸塩の製造方法 (2011)
  • Inventor(s): 佐藤美洋
  • Industrial Property Rights Holder: 日産化学工業
  • Industrial Property Number: 2011-187128
  • Filing Date: 2011-08-30